In early 2010, A.V. Club writer Nathan Rabin decided to listen to and write about the bestselling, zeitgeist-friendly CD series NOW That’s What I Call Music! in chronological order. Each one of the 34 American NOW! collections compiles a cross-section of recent hits from across the musical spectrum. Beginning with the first entry from 1998, this column examines what the series says about the evolution and de-evolution of pop music.

With each entry in this series, I’ve aspired to write about more than a bunch of randomly selected pop songs. I’ve tried to use each entry as a starting point to discuss the careers and contradictions of the heroes of this pop age, such as Liz Phair, Justin Timberlake, Aaron Carter, Britney Spears, Britney Spears, and Britney Spears. As some of you have noted, I write an awful lot about Britney Spears. That’s because to me, she represents everything that’s seductive, ridiculous, surreal, wonderful, and sexy about pop music.

Just as I want every My Year Of Flops entry to be more than a movie review, I want THEN! to be more than a rundown of half-forgotten singles. Alas, the 15th entry in the series has defeated me. I couldn’t find a song or an artist fascinating enough to serve as an anchor for an entire entry, so I’m going to do something new: I’m going to write about every song in the volume.

1. No Doubt, “It’s My Life” When No Doubt began its ascent to superstardom, the band struck me less as a second- or third-wave ska band than as new-wave revivalists, the Missing Persons of its era. So it seems altogether apt that the group covered Talk Talk’s “It’s My Life” as the sole new track on its greatest-hits album The Singles 1992-2003. The result is one of my favorite No Doubt songs simply because the group understands how to get out of the way of a great song, and Gwen Stefani’s melodramatic vamping perfectly suits the anthem’s heightened emotions.

2. Britney Spears, “Toxic” The poorly kept secret of dance music is that the genre is so dependent on production and that fascist four-on-the-floor beat that vocals are sometimes irrelevant. Actually, vocals are overwhelmingly irrelevant. It doesn’t particularly matter, for example, whether Britney Spears or Kylie Minogue, who was originally offered the song, is breathily whispering the mildly salacious lyrics to “Toxic.”

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I admire “Toxic” as if it were a European sports car: I appreciate its sleekness, its impeccable engineering, the way every part is fine-tuned and perfectly in place. It’s a triumph of pop machinery, full of racing synthesizers, atmospheric strings, and a beat so infectious, it lodges itself into the human subconscious upon the first listen, then plants the squatters’-rights flag and refuses to leave.

The cultural baggage Spears brings to the song as a longtime participant in toxic relationships with widely reviled douchebags (Kevin Federline, cough, cough) gives it a little extra iconic kick, but mostly it succeeds on the strength of pure craft. Sexy, sexy craft.

3. Ludacris, “Stand Up”Ludacris, on the other hand, is all about personality. From a technical perspective, he’s tremendously gifted, with an elastic, wildly expressive flow, but his impeccable comic timing and incandescent charisma are what made him such a superstar. Take “Stand Up,” for example, one of his best songs and earliest collaborations with Kanye West. The song contains arguably the best line in the history of music, better even than anything in Shaggy’s “It Wasn’t Me.”

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At the beginning of Ludacris’ epic tale of nightclub debauchery, Ludacris propositions a potential conquest with the words “How we ain’t gonna fuck? Bitch, I’m me!” (the radio version changes it to “How you ain’t gonna cut? Girl, I’m me”) This is, clearly, the single greatest pickup line ever, though only people of Ludacris’ stature can get away with it. Men who have to follow “Bitch, I’m me!” with “You know, the guy who sits behind you in biology,” for example, will find it doesn’t work anywhere near as well.

4. Chingy featuring Ludacris and Snoop Dogg, “Holidae In”Alas, not even the combined star power of Ludacris and Snoop Dogg can save Chingy’s “Holidae In,” an inane bit of pop-rap fluff about the glory of taking groupies to modestly priced hotel chains. Also, judging from the lyrics, it’s unclear whether Chingy, Ludacris, and Snoop Dogg are planning to “feel on each other” or merely bask in the bisexuality of their (ostensibly female) orgy partners. Is “Holidae In” the worst song on the compilation? Perhaps, though it faces a fierce challenge from Nick Cannon and R. Kelly’s “Gigolo.” To settle the matter, let’s have the competitors compete in a high-stakes all-or-nothing terrible-off. Here are the respective choruses for the two songs:

“Holidae In”:

(Whachu doin?) Nothing, chillin’ at the Holidae Inn
(Who you wit?) Me and my peeps, won’t you bring four of your friends
(What we gon’ do?) Feel on each other and sip on some Hen
One thing leading to another, let the party begin.”

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“Gigolo”:

I’m a gigolo, spending lotsa dough
You can tell the way the wide-body’s sitting on vogues
Peep how I’m shining, wit’ the fresh, fresh clothes
Always surrounded by so many (HO!)
I’m a gigolo, always on the go
Every time I turn around, I got another show
Leave the club with about three in a row
Jump in the Six, ’cause I love them (HO!)

5. Westside Connection, “Gangsta Nation”Considering how his career has progressed, and his ubiquity in family fare, it’s downright adorable that Ice Cube still gets together with his friends and favored collaborators to make pretend that they’re still scary, gun-toting gangstas instead of wealthy middle-aged men who home-school their children and are more concerned with TBS picking up their family sitcom for 90 more episodes than surviving another day in the mean streets of South Central.

In 2003, Cube and his pals Mack 10 and W.C. reunited to release Terrorist Threats, an album of regressive ’90s-style G-funk rooted in a bygone era where Cube could legitimately consider himself AmeriKKKa’s Most Wanted rather than AmeriKKKa’s family actor of choice. On “Gangsta Nation,” Cube and the gang talk tough and posture, but Cube isn’t fooling anyone, least of all himself.

6. Sarah Connor, “Bounce”If Sarah Connor’s “Bounce” sounds awfully familiar, it’s for a very good reason: the song borrows the propulsive strings from Mary J. Blige’s Dr. Dre-produced smash “Family Affair” for one of the compilation’s many acid-tongued kiss-offs, this time to a cheating partner. For some reason, R&B songs that sample hip-hop songs piss me off, though I have no problem with hip-hop sampling R&B. Sampling soul takes imagination and a broad frame of reference; repurposing a 3-year-old song, on the other hand, just feels lazy, especially when it pales in comparison to the song it’s sampling.

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On “Bounce,” Connor zings a cheating lover who won’t answer his two-way or his pager, and consequently must be creeping with another woman, in spite of the impeccably oiled cleavage Connor displays in the music video. Connor’s reasoning isn’t terribly clear. At one point, she opines, “I know that you’re hating it, but you better stay with the one you’re with,” which is confusing on multiple levels. Is “the one you’re with” Connor? Or the woman the man is cheating on? Connor is clearly a keeper; the woman knows how to crawl on the hood of a car in an appropriately sensual fashion. In his guest verse, rapper Mr. Freeman pleads for another chance and volunteers, “I love it every night the freaky way we bone.” Mr. Freeman better shape up, or he’ll find himself with a lesser woman who’ll only bone him every other night, and only in a semi-freaky fashion.

7. Black Eyed Peas, “Shut Up” Most pop-music compilations are full of inane love songs. NOW! 15, in sharp contrast, is so full of bile, bruised feelings, and insults, I half-expected Mary J. Blige to pop up in the middle of “Bounce” and offer a Rodney King-like plea for an end to hateration and holleration up in this dancerie.

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On “Shut Up,” Will.I.Am and the other two guys discover that hell hath no fury like a Fergie scorned. At first, everything is copacetic: The happy couple did “them things that couples do when in love” such as “walks on the beach and stuff.” They also did “things that lovers say and do,” such as “I love you, boo” and also “I love you too.” Ah, but soon conflicts and disagreements arose. One party would say “I love you a lot,” the other would counter with “I love you even more.” But then infidelity transformed love into hate.

It goes without saying that “Shut Up” is a stupid song, but in our shiny pop world, stupidity isn’t necessarily a vice, and intelligence isn’t always a virtue. “Shut Up” is about as fun as the Black Eyed Peas get. It’s a cartoon battle of the genders, a sexual showdown complete with spaghetti-Western guitar and an appropriately theatrical turn from Fergie. At the risk of losing what little credibility I have left, Fergie is growing on me; her lyrics are almost inconceivably awful, but she has a hell of a voice, and, if I may damn her with some faint praise, she was easily the best part of Nine.

8. Nick Cannon, “Gigolo” How can a hit be a miss? When it’s as all-consumingly awful as Nick Cannon and R. Kelly’s “Gigolo,” a song that reached No. 24 on the Billboard, chart yet confirmed what everyone already knew: The former Nickelodeon star, best known for being Mr. Mariah Carey, has no fucking business pursuing a musical career. It’s a song of almost unspeakable banality, a lazy R. Kelly knockoff built around sugary flute, indifferently strummed acoustic guitar, and a generic breakbeat.

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The lyrics are as inane as the music, as Cannon and Kelly assert that they’re gigolos, as detailed above. By why take my word for it when you can experience the magic yourself? When Eminem took shots at Cannon’s wife, the multi-talentless Cannon jokingly threatened to return to rap to defend his wife’s honor. See, it’s funny, because even Cannon realizes he has no musical ability whatsoever.

9. Beyoncé, “Me, Myself And I”A lifetime ago, when I lived in a Madison co-op, one of my housemates said Pearl Jam’s “Better Man” gave her the courage to finally leave an unsatisfying relationship and a stale hometown, and move to another city in search of herself. I was still a cynical bastard at that point, so my housemate’s words struck me as self-aggrandizing, self-mythologizing collegiate horseshit. But on some level, I was moved. Our relationship with music is ferociously personal and emotional. I can definitely see Beyoncé’s self-esteem anthems having the same effect on young girls in dead-end relationships that Pearl Jam’s song did on my former housemate.

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If nothing else, this project has instilled in me a renewed admiration for Beyoncé as a singer, writer, and pop icon. “Me, Myself And I,” her ingratiatingly intimate contribution to NOW! 15,offers a subtle variation on what I have previously described as her core message: “I’m awesome. Fuck you.”

That message is often delivered with breathless force, as on “Independent Woman,” but on “Me, Myself And I,” she offers a kinder, gentler take on the theme. The attitude of the song is less “I’m awesome, fuck you” than “You’re a disappointment and unworthy of me, and I’m better off retreating into the defining relationship in my life: my ongoing love affair with myself.”

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Beyoncé’s spectacular excess of self-esteem can’t help but rub off on a largely young, largely female fan base that desperately needs her core message that women should value themselves and refuse to be treated with disrespect. And, it should be noted, “Me, Myself And I” is a pretty terrific song musically, a kiss-off with the softness, vulnerability, and beguiling tenderness of a ballad. God bless you, Beyoncé. I don’t care if you did perform at George W. Bush’s inauguration: You’re on the side of the angels as far as I’m concerned.

10. Baby Bash, “Shorty Doowop” On “Shorty Doowop,” a gentleman named Baby Bash expresses his appreciation for a young woman who has truly earned the designation of “Shorty Doowop,” which the good folks over at urbandictionary.com (an invaluable resource for doddering types looking to understand the oft-incomprehensible jive talk of today’s young people) helpfully defines as “a girl that you like or love or have a crush on. mostly are short. lol.” Only a small majority of users of the site agree with that definition, but I think the less-than-ringing endorsement has more to do with the entry’s horrifying grammar, lack of punctuation, and unconscionable use of puns and cyber-speak than anything else.

What did the woman in question do to earn Bash’s love? Let’s list her attributes, as demarcated by Mr. Bash’s lyrics:

She has won the love of all the players in Bash’s neighborhood/social circle.

She has a ready supply of marijuana for him to consume during their time together.

She stuck with Bash when he violated parole.

She accepted Bash’s collect calls from prison.

She believed in Bash when they had nothing.

She looks “so mighty mighty.”

She respects Bash when he’s good and loves him when he’s in trouble.

She’s looking throwed.

Above all, she is “the only boo” who “do the freaky things you do.”

Clearly an impressive woman. But what could have attracted this contemporary goddess to Bash beyond his evident charm, wit, and flair for language? According to the song, the woman “got with” him because her “hubby was a weirdo” and she appreciated that Bash is always “fresh and clean and so tighty.” These are intriguing, albeit maddeningly enigmatic clues to the woman’s identity. She’s married to an eccentric gentleman. Bobby Fischer, perhaps? Considering the premium this woman places on Bash’s superior hygiene, it would appear this gentleman is slovenly and indifferent to matters of personal appearance. Wavy Gravy? Tiny Tim? Maddeningly enigmatic lyrics aside, “Shorty Doowop” is a nifty guilty pleasure, bubblegum hip-hop/R&B with a buttery (though moronic) chorus and a throwback ’80s R&B vibe.

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I know I, and many others, look to NOW! compilations for information about instigating and sustaining romantic relationships, so I think it’s telling that in both “Shorty Doowop” and “Bounce,” a musician expresses appreciation for their partners specifically because of the “freaky” shit they do. This seems incongruous with Bash’s dismissal of his Shorty Doowop’s husband as a “weirdo,” but I think we can extrapolate Mr. Bash’s lyrics to suggest that he too wants to maintain a relationship because of the “freaky way” he and his shorty doowop “bone.” The takeaway is clear: If you want to hold onto your shorty doowop, you should make sure that you and your partner bone in a freaky fashion, but not to the extent where you will be derided as a “weirdo.” I think all y’all know what that means: fucking in ICP clown makeup, the 12-sided die, perhaps a position other than missionary. Use your imaginations, y’all.

11. Eamon, “I Don’t Want You Back” The artists of NOW! 15 sure are an angry, confrontational lot, aren’t they? First we’ve got Sarah Connor telling us to bounce, then Fergie telling us to shut up, then Beyoncé showing some non-bills-paying scrub the door, and now a British gentleman named Eamon delivering the blunt message “I Don’t Want You Back.” The song used to be even blunter: The original British version was indelicately titled “Fuck It (I Don’t Want You Back).”

That title didn’t prove palatable with radio programmers here in God’s own United States, though. Nor did other provocative Eamon singles with titles like “Stupid Cunt (Why Did You Have to Hurt Me?)” and “Shitty Fucking Piece Of Shit Girlfriend (Getting Over You).” Alas, “Fuck It (I Don’t Want You Back)” is a provocative title for a dishwater-dull slab of sleepy synthesizers and a tepid drumbeat that relies almost entirely on the transgressive shock and incongruity of Eamon uttering the words “fuck,” “shit,” “ho,” and “bitch” something like 30 times while crooning what only sounds like a maudlin ballad.

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The American single/radio version completely destroys everything that’s distinctive, funny, nasty, and subversive about the single, transforming a howl of rage into petulant, whiny self-pity. The uncensored version is a stirring tribute to profanity’s visceral power, whereas the radio version is a joke without a punchline. The song was so popular that it inspired “F.U.R.B. (FU Right Back),” an answer song by Frankee, an upstart who claims the song was written about her, when we all know it was written about both Roxanne Shanté and UTFO.

12. Jessica Simpson, “With You” “With You” addresses a ubiquitous theme in pop music, particularly the oeuvre of Jennifer Lopez: the contrast between the public and private, the glossy persona and the squirmy human being underneath. See, y’all probably see Simpson on the big and little screen and think she’s like that 24/7. But she isn’t!

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According to her love song/manifesto “With You,” the real Simpson is a “Southern girl with her Levis on and an open heart.” (Andrew “Dice” Clay: “And some open legs, ooooh!!!”) The real J. Simp “used to laugh all night, lying in the grass, just talking ’bout love.” But then stardom hit and she got jaded, and life got Denise Richards-level complicated.

It’s true. For years, Simpson was notorious for showing up at Hollywood soirées in a black beret and turtleneck, smoking clove cigarettes, drinking absinthe, and discoursing wittily and apathetically about the emptiness of contemporary society and the futility of all human endeavor. She sneered at a world she considered beneath her, protected by a cocoon of inflated self-regard.

Simpson can only return to the Eden of her pre-jaded phase in the comforting, consoling arms of a lover who accepts her as she is, a down-to-Earth Texas gal as well as a world-famous multi-millionaire sex symbol. Of course, “With You” is cloying and schmaltzy, but Simpson sings with a winning vulnerability, and there’s something oddly touching about her homage to the liberating powers of unconditional love.

13. Norah Jones, “Sunrise” From the ridiculous to the sublime. Norah Jones’ “Sunrise” sounds like sex: smoky, sensual, and as satisfyingly languid as a post-coital nap. It’s jazz. It’s soul. It’s slow-burning pop. What’s a classy girl like Jones doing in a place like this?

14. Sheryl Crow, “The First Cut Is The Deepest” See track one.

15. Fefe Dobson, “Everything”Since the eureka moment when Sam Phillips realized he could make a fortune with a white man who sang black, the music world has historically gone nuts over attractive blue-eyed soul men and women (blue-eyed soulpeople?) Fefe Dobson represents the antithesis of this phenomenon: She’s a lovely, light-skinned black woman who sings uncannily like a really boring white secretary-rocker in the Sheryl Crow vein.

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Like many secretary-rockers before her, from Meredith Brooks to Jennifer Love Hewitt to Alanis Morissette, Dobson is all about listing things. Here we learn that

Sometimes Dobson gives into sadness.

Sometimes she don’t.

At times she’s part of the madness.

Sometimes she won’t (give into you).

At times she feels herself smiling.

At times she’s not (smiling, apparently).

Sometimes she feels like a nut.

Sometimes she don’t.

Dobson broke down barriers. Verily, she’s the Jackie Robinson of bland middle-of-the-road VH1 pop. Regardless of what you think about Dobson—and sweet blessed Lord, does she invite some mild emotions—we can all agree that she has, arguably, the greatest The Perfect Score-themed video ever. Remember that movie? Me neither.

16. Three Days Grace, “I Hate Everything About You” The band Three Days Grace has much to answer for: its terrible name, its terrible music, and its terrible decision to give its contribution to NOW! 15 the same terrible title as a terrible hit by a terrible ’90s band. Yes, I dislike all the elements of this song: the hunger-dunger-dang bleating, the overwrought lyrics, the grunge-by-numbers power chords, and especially the ham-fisted quasi-irony of a chorus yelling, “I hate everything about you! Why do I love you?” Somewhere, Ugly Kid Joe is spinning in his grave.

17. Blink-82, “Feeling This” Oh boy, our pals in Blink-182 are back, and they’re totally excited about going on a date with a girl! They might even get to third or fourth or the little-known fifth base! The butterflies! The excitement! So adorable! The nerves! Haven’t we heard this song/seen this video several times before? Yes. Yes, we have.

18. Good Charlotte, “Hold On” Good Charlotte’s “Hold On” is such a dour, joyless song that it took several listens for me to realize that it’s supposed to be inspirational. Heck, it’s supposed to be more than educational: It’s supposed to keep suicidal fans from giving it all up and heading to the great Warped Tour in the sky, where all the roadies are angels and everyone’s getting laid every single night.

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Yes, the Maddens want you to step back from that ledge, my friend, Third Eye Blind-style. It’s an important message powerfully conveyed by the music video, though the song is more of a bummer than a pick-me-up.

19. Fuel, “Falls On Me” Fuck you, Fuel. You suck.

20. Five For Fighting, “100 Years”There’s a subgenre of music I like to call Dawson’s Creek rock. It seems to have been made specifically to accompany montages of overly sensitive young people staring wistfully, thoughtfully into the distance while contemplating a romantic crisis in a teen soap opera on WB or UPN. Last volume’s “Why Can’t I?” fit snugly into this paradigm, as does Five For Fighting’s epically wusstastic “100 Years.” If the fellas made the song specifically for TV, they succeeded spectacularly, as it provided musical wallpaper for Smallville, JAG, Scrubs,and One Tree Hill. Mission accomplished! What a triumph of wussiness! “100 Years” is so wimpy that even “Sunrise” shoved it into a locker and gave it a wedgie. “100 Years” is the “It Was A Very Good Year” of maudlin crap.

Up next on THEN!: Andre 3000 wants you to shake it like a Polaroid picture, Eminem is kind of hurt that you don’t even know the name of his band, and Juvenile and Soulja Slim want to see you to grind in slow-motion for them.

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Outside the bubble: What else was going on musically in spring 2004:

Aerosmith releases the covers album Honkin’ On Bobo. The world is not impressed.